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MischiefPup

@mischiefpup.bsky.social
1.1K followers 1.7K following 156 posts

(he/him) Diaper Boi🍼, (Big) Dildo Enthusiast🍆, Pain Puppy🐶, Leather 😵‍💫, D&D🐉🧙‍♂️, Kayaker 🛶 📍 Chicago, IL

PostsRepliesMedia
MischiefPup @mischiefpup.bsky.social · 18/09/2026
Try saying LeatherLittle 3 times fast. That's right, you can't! Cause I'm a big boy that's why! *finger guns* 😎 Pew Pew!
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MischiefPup @mischiefpup.bsky.social · 22/08/2026
Yeah I had a little accident, but it sure feels pretty good. 😎
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MischiefPup @mischiefpup.bsky.social · 15/08/2026
You can have this cake and eat it too!🍰 This puppy needs to get dicked down until he doesn't remember thoughts 😵‍💫😵‍💫
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MischiefPup @mischiefpup.bsky.social · 04/08/2026
It's funny what 2 weeks without cumming and some bullying from @littlezap.bsky.social will do to a sub. Huffing sweaty socks and uncaged but clearly better off locked up. What a loser!
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MischiefPup @mischiefpup.bsky.social · 27/07/2026
What do you say we call off work, kit up, and go kick the ball(s) around?
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MischiefPup @mischiefpup.bsky.social · 02/07/2026
No need to check me! The outdoor furniture is waterproof so it's all good bro! Unless you're tryna do some snoofin 😏
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MischiefPup @mischiefpup.bsky.social · 20/06/2026
"Loons just have a charisma that people can't resist." -NPR WHAT is my donation funding?! 🤣🤣🤣🤣
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MischiefPup @mischiefpup.bsky.social · 12/06/2026
Let's see if I can't fuck the cum outta myself.
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MischiefPup @mischiefpup.bsky.social · 02/06/2026
Am I the top dog, or did you just drop the leash? 😏 Hat by @mistrbear.bsky.social Shirt by @cockeyekink.bsky.social Harness by @mrsleather.bsky.social #SexDog #Awoo #Awoof #Bark #Bork
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MischiefPup @mischiefpup.bsky.social · 25/05/2026
There's no better way to relax after a wonderfully busy and exceptionally great IML than by breaking in the new toy from @friendlytoys.ca 😈 😵‍💫
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MischiefPup @mischiefpup.bsky.social · 06/05/2026
Welcome.....to Jurassic Park! 🦕 🦖 #DiapersInNature #SoggyBackpacking #CatchMeOutsideHowBoutDat
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MischiefPup @mischiefpup.bsky.social · 24/04/2026
Lé Whorè du Outdoorés Before & After
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MischiefPup @mischiefpup.bsky.social · 12/04/2026
Hello Lake Michigan! It only says dogs have to be on a leash! There's nothing about wearing pants....or cages! 😈
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MischiefPup @mischiefpup.bsky.social · 07/04/2026
I have NO IDEA how this happened!!! I was being a good boy, minding my own business, and then... 💥BAM💥....I got bred! Heh! Bred. See what I did there. 😉
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MischiefPup @mischiefpup.bsky.social · 02/04/2026
You wanna feel the squish, bruh? 😈
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MischiefPup @mischiefpup.bsky.social · 15/03/2026
Help me out coach! I can't figure out how I'm supposed to wear this thing! I'm just tryna be a good athletic supporter!
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MischiefPup @mischiefpup.bsky.social · 09/03/2026
Step into my office bub. That's right, I can both pee my pamps AND run the office. I'm pretty talented if I do say so myself.
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MischiefPup @mischiefpup.bsky.social · 18/02/2026
Sitting on the floor trying to pick out clothes for my first trip back to the office. Am I a big boy? Athletic boy? Just need a little help with potty training? Or do I need the real big, thick, diapers?? 🤔🤔
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MischiefPup @mischiefpup.bsky.social · 11/02/2026
Occasionally, when left unsupervised, dogs can get caught in their own trap!!! Would you help me escape? Or are you gonna take control of the hypno and the nipple clamps and keep a pup on edge? 😈 😈 😈
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MischiefPup @mischiefpup.bsky.social · 07/02/2026
When he says 'I've been getting into working my hole with toys.' Come on over pup, we'll put your hole to work, and leave you agape! 😈
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MischiefPup @mischiefpup.bsky.social · 05/02/2026
*barista voice* I have a Gingerbread iced latte for a....Locked Boi!
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MischiefPup @mischiefpup.bsky.social · 26/01/2026
TREAT! No Treat. TREAT! No Treat. TREAT! No Treat. Awwwwwwwww 🐶. 🤫 I got the treat anyway 🤫
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MischiefPup @mischiefpup.bsky.social · 26/01/2026
Breaking News Local dog spotted enjoying his iced coffee while growling at latest 'monster storm' More at 11
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MischiefPup @mischiefpup.bsky.social · 22/01/2026
From fresh and dry to soaked and absolutely wrecked. 19 hrs of pure, unadulterated, sogging! 🫣🫣🫣 My first Little Kings was a success!! And there is something about the design on cloth that unexpectedly brought out the little in me.
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MischiefPup @mischiefpup.bsky.social · 18/01/2026
What's the sound? Is it the breathing machine pumping in poppers? Or maybe it's the hum of the electro box as @crewbiker.bsky.social ticked up the power flowing through my nipples until I was a gooned out little pain pup. 🤷‍♂️ Either way it ended with no cum and some extremely sensitive nipples
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MischiefPup @mischiefpup.bsky.social · 12/01/2026
Just a dog, who supports the dogs out there who play sports!!! Finally got my @theicedogs.bsky.social jersey and it's perfect!
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MischiefPup @mischiefpup.bsky.social · 10/01/2026
It's Saturday that means we can go outside right?! Lezz go! I'm ready! Awooooooooo!!! *wags*
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MischiefPup @mischiefpup.bsky.social · 07/01/2026
Dinner! presented by Dog! Awoooooo!!! Spinach pasta with a creamy parmesan and mushroom sauce with grilled chicken! *wags*
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MischiefPup @mischiefpup.bsky.social · 28/12/2025
Merry Cribmus and Happy Toyota-thon 🐶 Love you all, see you in 2026 ✌️
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MischiefPup @mischiefpup.bsky.social · 22/12/2025
Good dogs don't need to breathe 🥴
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MischiefPup @mischiefpup.bsky.social · 16/12/2025
I don't have anything groundbreaking to say...I just liked how my abs looked this morning. 😘 Day 18 so far. Maybe it'll stay on for the rest of the year with all the holiday chaos 🤷‍♂️
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MischiefPup @mischiefpup.bsky.social · 14/11/2025
Good morning boys, dogs, gimps, and fags. I'm feelin spicy today so who's gonna be a good boy and arch their back so I can watch their butt wiggle while I drink my coffee?
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MischiefPup @mischiefpup.bsky.social · 11/11/2025
Monday...consider it SOAKED! 😎
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MischiefPup @mischiefpup.bsky.social · 22/10/2025
What a compromising position to be caught in! 😱 Oh no! First time trying out the whole 'mouth stuffed with a bandana and then duct taped' it was actually quite nice 👌 And yes, @sirmf1.bsky.social was standing by to take the bag off my head as needed 😎 Hashtag SafetyFirstBonersSecond
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MischiefPup @mischiefpup.bsky.social · 16/10/2025
Cage and Coffee, not a Key in sight! Happy Locktober 16th everyone! I certainly havent made it all 16 days 😖 but that's okay! Remember, it's not about doing what everyone else is doing, it's about doing things that make you happy, and feel goooooood. 😏
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MischiefPup @mischiefpup.bsky.social · 06/10/2025
OMG!!! I was there! It was a really snug nap. 😴
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MischiefPup @mischiefpup.bsky.social · 03/10/2025
Locktober?? But what if.....I'm just sayin'....the key is just right there.... 👉👈
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MischiefPup @mischiefpup.bsky.social · 29/09/2025
Trying something new. Got this at the Leather Archives annual rummage sale. Not a skirt kind of kiddo, but I do like the Roman/Spartan look of it 🤔 I'm open to your tho(ugh)ts, checks, snoofs, and knee bouncies.
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MischiefPup @mischiefpup.bsky.social · 19/09/2025
Join me in the hot tub???
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MischiefPup @mischiefpup.bsky.social · 12/09/2025
Sometimes, even the Big Pups have accidents! But...maybe you should put your face in there, just to check 🤷‍♂️ Hashtag Oops-I-Wet-My-Jock
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MischiefPup @mischiefpup.bsky.social · 22/08/2025
I've been on a real diaper kick lately 🤷‍♂️ It's comfort in a stressful time. 🙂 Anyway, here's how I started the day on BigDiaperFriday™️ I absolutely wrecked this thing. Waking up warm and soggy sorta melts my mind and makes me feel like the littlest puppy. 🥹
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MischiefPup @mischiefpup.bsky.social · 18/08/2025
Wrapping up Soggy Sunday like a champ! Soaked, Soggy, Squishy, and Squirmy!
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MischiefPup @mischiefpup.bsky.social · 15/08/2025
Just PEEKing in to check on all y'all! 🤣🤣🤣
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MischiefPup @mischiefpup.bsky.social · 10/08/2025
Sometimes you just need to relax, breathe, and let the pain cleanse your mind. 😎 Thanks @crewbiker.bsky.social for quite a nice evening. Also I absolutely love all the color in this photo!
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MischiefPup @mischiefpup.bsky.social · 23/07/2025
Good morning dogs & degenerates! I found this tea here. Is yours? ..... Is mine?? Is okay anyway, can I has sips? Awwrrrrrrrrr! 🐶
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MischiefPup @mischiefpup.bsky.social · 15/07/2025
I've somehow ended up in this Dom Bottom era and I'm leaning in to it. So....just cause I'm locked up, just because I'm riding you, none of this means you get to cum. 😈
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MischiefPup @mischiefpup.bsky.social · 08/07/2025
It's called 'working out' and apparently it makes dogs big and strong. The big gym bros keep saying that I've gotta be naked and wear this silly cage on my weiner. 🤷‍♂️ They know what they're doing though......right.........right?! 🥹
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MischiefPup @mischiefpup.bsky.social · 18/06/2025
You can't keep the puppy outta the summer! Went to the first street fest of the season! Was a good enough boi that I got a sticker!
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MischiefPup @mischiefpup.bsky.social · 17/06/2025
Took a nap Jerked off Ate a torta from the street vendor, Had a crisp can of coke Watched the birds from the balcony A perfect night. 👌
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MischiefPup @mischiefpup.bsky.social · 28/05/2025
Okay....to all you wetsuit pups.....I get it. Puppy got a new wetsuit for summer activities.
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